5-Nitro-2-(trifluoromethoxy)benzenemethanol → (5-Amino-2-trifluoromethoxy-phenyl)-methanol

HRID 1819399Notes

Reaction equation

HRID 1819399 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:12][C:13]([F:16])([F:15])[F:14])=[C:8]([CH2:10][OH:11])[CH:9]=1)([O-])=O>CCOC(C)=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:12][C:13]([F:14])([F:15])[F:16])=[C:8]([CH2:10][OH:11])[CH:9]=1

Participants

3

Reactant 1

HCID 578857675-Nitro-2-(trifluoromethoxy)benzenemethanol

Product 1

HCID 22311140(5-Amino-2-trifluoromethoxy-phenyl)-methanolYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5-Nitro-2-trifluoromethoxy-phenyl)-methanol (2 g, 8.4 mmol) was dissolved in EtOAc (50 mL) and was degassed. Pd/C (200 mg) was then added and the mixture was degassed again. The solution was hydrogenated with a balloon for 3 h. After the reaction was complete, the solution was filtered through diatomaceous earth and the residue was chromatographed with 95:5 CH2Cl2:MeOH as an eluent to give 1.67 g (96%) of (5-amino-2-trifluoromethoxy-phenyl)-methanol as a yellow solid.

Workup

  1. customwas degassed
  2. additionPd/C (200 mg) was then added
  3. customthe mixture was degassed again
  4. filtrationthe solution was filtered through diatomaceous earth
  5. customthe residue was chromatographed with 95:5 CH2Cl2

Sources & evidence

ORD record
ord-094e1a4a5efc4127a7191eab26eb4bb2
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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